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US8637534B2 - Fungicide active substance combinations - Google Patents

Fungicide active substance combinations Download PDF

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Publication number
US8637534B2
US8637534B2 US12/481,947 US48194709A US8637534B2 US 8637534 B2 US8637534 B2 US 8637534B2 US 48194709 A US48194709 A US 48194709A US 8637534 B2 US8637534 B2 US 8637534B2
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United States
Prior art keywords
active compound
formula
weight
parts
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related, expires
Application number
US12/481,947
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US20090306109A1 (en
Inventor
Stefan Dutzmann
Klaus Stenzel
Manfred Jautelat
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Bayer CropScience AG
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Bayer Intellectual Property GmbH
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Priority to US12/481,947 priority Critical patent/US8637534B2/en
Publication of US20090306109A1 publication Critical patent/US20090306109A1/en
Priority to US13/786,295 priority patent/US20130296389A1/en
Assigned to BAYER INTELLECTUAL PROPERTY GMBH reassignment BAYER INTELLECTUAL PROPERTY GMBH DOCUMENT EVIDENCING ASSIGNMENT Assignors: BAYER CROPSCIENCE AG
Priority to US14/075,149 priority patent/US9253982B2/en
Application granted granted Critical
Publication of US8637534B2 publication Critical patent/US8637534B2/en
Priority to US14/979,997 priority patent/US20160106105A1/en
Assigned to BAYER CROPSCIENCE AKTIENGESELLSCHAFT reassignment BAYER CROPSCIENCE AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAYER INTELLECTUAL PROPERTY GMBH
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
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    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
    • A—HUMAN NECESSITIES
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
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    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • A—HUMAN NECESSITIES
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    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms

Definitions

  • the present invention relates to novel active compound combinations which consist of the known 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione and further known fungicidally active compounds, and which are highly suitable for controlling phytopathogenic fungi.
  • the fungicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the activities of the individual active compounds.
  • an unforeseeable, true synergistic effect is present, and not just an addition of activities.
  • the formula (II) includes the compounds
  • the formula (IV) includes the aniline derivatives of the formulae
  • the active compound of the formula (V) has three asymmetrically substituted carbon atoms.
  • the product may therefore be present as a mixture of various isomers, or else in the form of a single component. Particular preference is given to the compounds
  • the formula (VII) includes the compounds
  • the formula (XVI) includes the compounds
  • the formula (XXI) includes the compounds
  • the guanidine derivative of the formula (XXV) is a mixture of substances of the common name guazatine.
  • the active compound combinations according to the invention comprise at least one active compound of the compounds of groups (1) to (24). Additionally, they may comprise further fungicidally active components.
  • the synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios.
  • the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general,
  • the active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
  • the active compound combinations according to the invention are particularly suitable for controlling cereal diseases, such as Erysiphe, Puccinia and Fusarium , and for controlling diseases encountered in viticulture, such as Uncinula, Plasmopara and Botrytis , and furthermore in dicotyledonous crops for controlling powdery and downy mildew fungi and causative organisms of leaf spot.
  • cereal diseases such as Erysiphe, Puccinia and Fusarium
  • diseases encountered in viticulture such as Uncinula, Plasmopara and Botrytis
  • dicotyledonous crops for controlling powdery and downy mildew fungi and causative organisms of leaf spot.
  • the fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • the active compound combinations according to the invention can be employed for foliar application or else as seed dressings.
  • the active compound combinations according to the invention can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
  • formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers.
  • extenders that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers.
  • surfactants that is emulsifiers and/or dispersants, and/or foam formers.
  • the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents.
  • suitable liquid solvents include: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohe
  • Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates.
  • Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
  • Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl-sulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates.
  • Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and prussian blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments for example iron oxide, titanium oxide and prussian blue
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally comprise between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention can be present as a mixture with other known active compounds such as fungicides, insecticides, acaricides and herbicides, and as mixtures with fertilizers or plant growth regulators.
  • the active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting.
  • the application rates can be varied within a relatively wide range, depending on the kind of application.
  • the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha.
  • the application rates of the active compound combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.
  • the good fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities.
  • a synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
  • the expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15, (1967), 20-22).
  • X is the efficacy when applying active compound A at an application rate of m g/ha
  • Y is the efficacy when applying active compound B at an application rate of n g/ha
  • E is the efficacy when applying the active compounds A and B at an application rate of m and n g/ha,
  • the efficacy is calculated in %. 0% is an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • the activity of the combination is superadditive, i.e. a synergistic effect exists.
  • the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.
  • active compound or active compound combination 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • active compound or active compound combination 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at about 21° C. and a relative atmospheric humidity of about 90%.
  • Evaluation is carried out 12 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • active compound or active compound combination 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • active compound or active compound combination 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration,
  • the plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • active compound or active compound combination 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • active compound or active compound combination 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • active compound or active compound combination 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
  • the plants are sprayed with a spore suspension of Leptosphaeria nodorum .
  • the plants remain in an incubation cabin at 20° C. and 100% relative atmospheric humidity for 48 hours.
  • the plants are then placed in a greenhouse at a temperature of about 15° C. and a relative atmospheric humidity of about 80%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • active compound or active compound combination 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
  • the plants remain in an incubation cabin at 20° C. and 100% relative atmospheric humidity for 24 hours.
  • the plants are then placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of rust pustules.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • the active compounds are applied as a dry seed dressing. This is prepared by extending the respective active compound or the active compound combination with ground minerals to give a finely pulverulent mixture which ensures uniform distribution on the seed surface.
  • the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.
  • 2 ⁇ 100 corns of wheat are sown at a depth of 1 cm in standard soil and cultivated in a greenhouse at a temperature of about 18° C. and a relative atmospheric humidity of about 95% in seed trays which receive a light regimen of 15 hours per day.
  • the active compounds are applied as a dry seed dressing. This is prepared by extending the respective active compound or the active compound combination with ground minerals to give a finely pulverulent mixture which ensures uniform distribution on the seed surface.
  • the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.
  • 2 ⁇ 100 corns of wheat are sown at a depth of 1 cm in standard soil and cultivated in a greenhouse at a temperature of about 10° C. and a relative atmospheric humidity of about 95% in seed trays which receive a light regimen of 15 hours per day.
  • the active compounds are applied as a dry seed dressing. This is prepared by extending the respective active compound or the active compound combination with ground minerals to give a finely pulverulent mixture which ensures uniform distribution on the seed surface.
  • the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.
  • 2 ⁇ 50 corns of seed are sown at a depth of 2 cm in standard soil infected with Rhizoctonia solani , and the seeds are cultivated in a greenhouse at a temperature of about 22° C. in seed trays which receive a light regimen of 15 hours per day.

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Abstract

The novel active compound combinations comprising 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione of the formula
Figure US08637534-20140128-C00001
and the active compound of groups (1) to (24) listed in the description have very good fungicidal properties.

Description

This application is a divisional of U.S. application Ser. No. 09/843,396, filed Apr. 26, 2001 which is a divisional of U.S. application Ser. No. 09/402,866, filed Oct. 13, 1999, which is the national stage of International Application No. PCT/EP98/01986, filed Apr. 6, 1998, which claims priority to German Patent Application No. 197 16 257, filed Apr. 18, 1997.
The present invention relates to novel active compound combinations which consist of the known 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione and further known fungicidally active compounds, and which are highly suitable for controlling phytopathogenic fungi.
It is already known that 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione has fungicidal properties (cf. WO 96-16 048). The activity of this compound is good, however, at low application rates it is in some cases not satisfactory.
Furthermore, it is already known that a large number of triazole derivatives, aniline derivatives, dicarboximides and other heterocycles can be employed for controlling fungi (cf. EP-A 0 040 345, DE-A 2 201 063, DE-A 2 324 0 10, Pesticide Manual, 9th Edition (1991), pages 249 and 827, U.S. Pat. No. 3,903,090 and EP-A 0 206 999). Likewise, the activity of these compounds is not always satisfactory at loss application rates.
Finally, it is also known that 1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine can be used for controlling animal pests such as insects (cf. Pesticide Manual, 9th Edition (1991), page 491). However, fungicidal properties have not hitherto been described for this compound.
It has now been found that the novel active compound combinations comprising 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione of the formula
Figure US08637534-20140128-C00002
    • and (1) a triazole derivative of the formula
Figure US08637534-20140128-C00003
    • in which
    • X represents chlorine or phenyl
    • and
    • Y represents
Figure US08637534-20140128-C00004
    • and/or
    • (2) the triazole derivative of the formula
Figure US08637534-20140128-C00005
    • and/or
    • (3) an aniline derivative of the formula
Figure US08637534-20140128-C00006
    • in which
    • R1 represents hydrogen or methyl,
    • and/or
    • (4) N-[1-(4-chloro-phenyl)-ethyl]-2,2-dichloro-1-ethyl-3-methyl-cyclopropane-carboxamide of the formula
Figure US08637534-20140128-C00007
    • and/or
    • (5) the zinc propylene-1,2-bis-(dithiocarbamate) of the formula
Figure US08637534-20140128-C00008
    • n>=1
    • and/or
    • (6) at least one thiocarbamate of the formula
Figure US08637534-20140128-C00009
    • Me=Zn or Mn or a mixture of Zn and Mn
    • and/or
    • (7) the aniline derivative of the formula
Figure US08637534-20140128-C00010
    • and/or
    • (8) the compound of the formula
Figure US08637534-20140128-C00011
    • and/or
    • (9) the benzothiadiazole derivative of the formula
Figure US08637534-20140128-C00012
    • and/or
    • (10) the 8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxaspiro-[5,4]-decane of the formula
Figure US08637534-20140128-C00013
    • and/or
    • (11) the compound of the formula
Figure US08637534-20140128-C00014
    • and/or
    • (12) the compound of the formula
Figure US08637534-20140128-C00015
    • and/or
    • (13) the compound of the formula
Figure US08637534-20140128-C00016
    • and/or
    • (14) the dicarboximide of the formula
Figure US08637534-20140128-C00017
    • and/or
    • (15) a pyrimidine derivative of the formula
Figure US08637534-20140128-C00018
    • in which
    • R2 represents methyl or cyclopropyl,
    • and/or
    • (16) the phenyl derivative of the formula
Figure US08637534-20140128-C00019
    • and/or
    • (17) the morpholine derivative of the formula
Figure US08637534-20140128-C00020
    • and/or
    • (18) the phthalimide derivative of the formula
Figure US08637534-20140128-C00021
    • and/or
    • (19) the phosphorus compound of the formula
Figure US08637534-20140128-C00022
    • and/or
    • (20) a phenylpyrrole derivative of the formula
Figure US08637534-20140128-C00023
    • in which
    • R3 and R4 each represent chlorine or together represent a radical of the formula —O—CF2—O—,
    • and/or
    • (21) the 1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine of the formula
Figure US08637534-20140128-C00024
    • and/or
    • (22) the phenylurea derivative of the formula
Figure US08637534-20140128-C00025
    • and/or
    • (23) the benzamide derivative of the formula
Figure US08637534-20140128-C00026
    • and/or
    • (24) a guanidine derivative of the formula
Figure US08637534-20140128-C00027
    • in which
    • m represents integers from 0 to 5
    • and
    • R5 represents hydrogen (17 to 23%) or the radical of the formula
Figure US08637534-20140128-C00028
    • have very good fungicidal properties.
Surprisingly, the fungicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the activities of the individual active compounds. Thus, an unforeseeable, true synergistic effect is present, and not just an addition of activities.
The 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione of the formula (I) is known (cf. WO 96-16 048). The compound can be present in the “thiono” form of the formula
Figure US08637534-20140128-C00029
    • or in the tautomeric “mercapto” form of the formula
Figure US08637534-20140128-C00030
For simplicity's sake, only the “thiono” form is given in each case.
The formula (II) includes the compounds
    • 1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butane-2-one of the formula
Figure US08637534-20140128-C00031
    • 1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of the formula
Figure US08637534-20140128-C00032
    • and
    • 1-(4-phenyl-phenoxy)-3,3-yl)-butan-2-ol of the formula
Figure US08637534-20140128-C00033
The formula (IV) includes the aniline derivatives of the formulae
Figure US08637534-20140128-C00034
It is evident from the formula for the active compound of the formula (V) that the compound has three asymmetrically substituted carbon atoms. The product may therefore be present as a mixture of various isomers, or else in the form of a single component. Particular preference is given to the compounds
N—(R)-[1-(4-chloro-phenyl)-ethyl]-(1S)-2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide of the formula
Figure US08637534-20140128-C00035
    • and
    • N—(R)-[1-(4-chloro-phenyl)-ethyl]-(1R)-2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide of the formula
Figure US08637534-20140128-C00036
The formula (VII) includes the compounds
    • (VIIa) Me=Zn (zineb)
    • (VIIb) Me=Mn (maneb)
    • and
    • (VIIc) mixture of (VIIa) and (VIIb) (mancozeb).
The formula (XVI) includes the compounds
    • (XVIa) R2═CH3 (pyrimethanil)
    • and
Figure US08637534-20140128-C00037
The formula (XXI) includes the compounds
    • 4-(2,3-dichlorophenyl)-pyrrole-3-carbonitrile of the formula
Figure US08637534-20140128-C00038
    • and
    • 4-(2,2-difluoro-1,3-benzodioxol-7-yl)-1H-pyrrole-3-carbonitrile of the formula
Figure US08637534-20140128-C00039
The guanidine derivative of the formula (XXV) is a mixture of substances of the common name guazatine.
The components which are present in the active compound combinations according to the invention in addition to the active compound of the formula (I) are also known. Specifically, the active compounds are described in the following publications:
(1) Compounds of the formula (II)
  • DE-A 2 201 063
  • DE-A 2 324 010
    (2) Compound of the formula (III)
  • EP-A 0 040 345
    (3) Compounds of the formula (IV)
  • Pesticide Manual, 9th Edition (1991) pages 249 and 827
    (4) Compound of the formula (V) and individual isomers thereof
  • EP-A 0 341 475
    (5) Compound of the formula (VI)
  • Pesticide Manual, 9th Edition (1991), page 726
    (6) Compounds of the formula (VII)
  • Pesticide Manual, 9th Edition (1991), pages 529, 531 and 866
    (7) Compound of the formula (VIII)
  • EP-A 0 339 418
  • (8) Compound of the formula (IX)
  • EP-A 0 472 996
    (9) Compound of the formula (X)
  • EP-A 0 313 512
    (10) Compound of the formula (XI)
  • EP-A 0 281 842
    (11) Compound of the formula (XII)
  • EP-A 0 382 375
    (12) Compound of the formula (XIII)
  • EP-A 0 515 901
    (13) Compound of the formula (XIV)
  • EP-A 196 02 095
    (14) Compound of the formula (XV)
  • U.S. Pat. No. 3,903,090
    (15) Compounds of the formula (XVI)
  • EP-A 0 270 111
  • EP-A 0 310 550
    (16) Compound of the formula (XVII)
  • Pesticide Manual, 9th Edition (1991), page 159
    (17) Compound of the formula (XVIII)
  • EP-A 0 219 756
    (18) Compound of the formula (XIX)
  • Pesticide Manual, 9th Edition (1991), page 431
    (19) Compound of the formula (XX)
  • Pesticide Manual, 9th Edition (1991), page 443
    (20) Compounds of the formula (XXI)
  • EP-A 0 236 272
  • EP-A 0 206 999
    (21) Compound of the formula (XXII)
  • Pesticide Manual, 9th Edition (1991), page 491
    (22) Compound of the formula (XXIII)
  • DE-A 2 732 257
    (23) Compound of the formula (XXIV)
  • EP-A 0 600 629
    (24) Substance of the formula (XXV)
  • Pesticide Manual, 9th Edition (1991), page 461
In addition to the active compound of the formula (I), the active compound combinations according to the invention comprise at least one active compound of the compounds of groups (1) to (24). Additionally, they may comprise further fungicidally active components.
The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general,
0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, of active compound of group (1),
0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, of active compound of group (2),
0.2 to 150 parts by weight, preferably 1 to 100 parts by weight, of active compound of group (3),
0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (4),
1 to 50 parts by weight, preferably 5 to 20 parts by weight, of active compound of group (5),
1 to 50 parts by weight, preferably 2 to 20 parts by weight, of active compound of group (6),
0.1 to 50 parts by weight, preferably 1 to 30 parts by weight, of active compound of group (7),
0.2 to 50 parts by weight, preferably 1 to 20 parts by weight, of active compound of group (8),
0.02 to 50 parts by weight, preferably 0.2 to 10 parts by weight, of active compound of group (9),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of group (10),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of group (11),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of group (12),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of group (13),
0.1 to 50 parts by weight, preferably 1 to 30 parts by weight, of active compound of group (14),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of group (15),
0.1 to 50 parts by weight, preferably 2 to 20 parts by weight, of active compound of group (16),
1 to 20 parts by weight, preferably 2 to 10 parts by weight, of active compound of group (17),
1 to 50 parts by weight, preferably 2 to 20 parts by weight, of active compound of group (18),
1 to 50 parts by weight, preferably 2 to 20 parts by weight, of active compound of group (19),
0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (20),
0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight, of active compound of group (21),
0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (22),
0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (23),
and/or
0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (24)
are present per part by weight of active compound of the formula (I).
The active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
The active compound combinations according to the invention are particularly suitable for controlling cereal diseases, such as Erysiphe, Puccinia and Fusarium, and for controlling diseases encountered in viticulture, such as Uncinula, Plasmopara and Botrytis, and furthermore in dicotyledonous crops for controlling powdery and downy mildew fungi and causative organisms of leaf spot.
The fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. The active compound combinations according to the invention can be employed for foliar application or else as seed dressings.
The active compound combinations according to the invention can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
These formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents include: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl-sulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and prussian blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%.
In the formulations, the active compound combinations according to the invention can be present as a mixture with other known active compounds such as fungicides, insecticides, acaricides and herbicides, and as mixtures with fertilizers or plant growth regulators.
The active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting.
When using the active compound combinations according to the invention, the application rates can be varied within a relatively wide range, depending on the kind of application. In the treatment of parts of plants, the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In the treatment of seeds, the application rates of the active compound combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.
The good fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities.
A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
The expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15, (1967), 20-22).
If
X is the efficacy when applying active compound A at an application rate of m g/ha,
Y is the efficacy when applying active compound B at an application rate of n g/ha
and
E is the efficacy when applying the active compounds A and B at an application rate of m and n g/ha,
then
E = X + Y - X · Y 100
The efficacy is calculated in %. 0% is an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.
The examples that follow illustrate the invention.
EXAMPLE 1
Sphaerotheca Test (cucumber)/protective
Solvent: 47 parts by weight of acetone
Emulsifier:  3 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at about 23° C. and a relative atmospheric humidity of about 70%.
Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below.
TABLE 1
Sphaerotheca test (cucumber)/protective
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00040
 		2.5 0.5 21  0
Figure US08637534-20140128-C00041
 		25    0
Figure US08637534-20140128-C00042
 		25    0
Figure US08637534-20140128-C00043
 		25    0
Figure US08637534-20140128-C00044
 		25    0
Figure US08637534-20140128-C00045
 		25    0
Figure US08637534-20140128-C00046
 		50    0
Figure US08637534-20140128-C00047
 		25    0
Figure US08637534-20140128-C00048
 		25    0
Figure US08637534-20140128-C00049
 		25    0
Figure US08637534-20140128-C00050
 		12.5   0
Figure US08637534-20140128-C00051
 		12.5   0
Figure US08637534-20140128-C00052
 		12.5   0
Figure US08637534-20140128-C00053
 		12.5   0
Figure US08637534-20140128-C00054
 		12.5   0
Figure US08637534-20140128-C00055
 		2.5 57
Figure US08637534-20140128-C00056
 		2.5 59
Figure US08637534-20140128-C00057
 		12.5  13
Figure US08637534-20140128-C00058
 		2.5  0
Figure US08637534-20140128-C00059
 		2.5 50
Figure US08637534-20140128-C00060
 		2.5 37
Figure US08637534-20140128-C00061
 		2.5 80
Figure US08637534-20140128-C00062
 		2.5 22
Figure US08637534-20140128-C00063
 		2.5  0
According to the invention: found calc *)
Figure US08637534-20140128-C00064
Figure US08637534-20140128-C00065
 		70 21
Figure US08637534-20140128-C00066
Figure US08637534-20140128-C00067
 		63 21
Figure US08637534-20140128-C00068
Figure US08637534-20140128-C00069
 		63 21
Figure US08637534-20140128-C00070
Figure US08637534-20140128-C00071
 		63 21
Figure US08637534-20140128-C00072
Figure US08637534-20140128-C00073
 		59 21
Figure US08637534-20140128-C00074
Figure US08637534-20140128-C00075
 		52 21
Figure US08637534-20140128-C00076
Figure US08637534-20140128-C00077
 		63 21
Figure US08637534-20140128-C00078
Figure US08637534-20140128-C00079
 		59 21
Figure US08637534-20140128-C00080
Figure US08637534-20140128-C00081
 		52 21
Figure US08637534-20140128-C00082
Figure US08637534-20140128-C00083
 		50 21
Figure US08637534-20140128-C00084
Figure US08637534-20140128-C00085
 		63 21
Figure US08637534-20140128-C00086
Figure US08637534-20140128-C00087
 		50 21
Figure US08637534-20140128-C00088
Figure US08637534-20140128-C00089
 		75 21
Figure US08637534-20140128-C00090
Figure US08637534-20140128-C00091
 		54 21
Figure US08637534-20140128-C00092
Figure US08637534-20140128-C00093
 		80 57
Figure US08637534-20140128-C00094
Figure US08637534-20140128-C00095
 		75 59
Figure US08637534-20140128-C00096
Figure US08637534-20140128-C00097
 		66 31
Figure US08637534-20140128-C00098
Figure US08637534-20140128-C00099
 		90 21
Figure US08637534-20140128-C00100
Figure US08637534-20140128-C00101
 		85 61
Figure US08637534-20140128-C00102
Figure US08637534-20140128-C00103
 		90 50
Figure US08637534-20140128-C00104
Figure US08637534-20140128-C00105
 		93 84
Figure US08637534-20140128-C00106
Figure US08637534-20140128-C00107
 		70 38
Figure US08637534-20140128-C00108
Figure US08637534-20140128-C00109
 		52 21
found = efficacy found
calc. = efficacy calculated using the Colby formula
EXAMPLE 2
Venturia Test (Apple)/Protective
Solvent: 47 parts by weight of acetone
Emulsifier:  3 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous konidia suspension of the causative organism of apple scab Venturia inaequalis and then remain in an incubation cabin at about 20° C. and 100% relative atmospheric humidity for one day.
The plants are then placed in a greenhouse at about 21° C. and a relative atmospheric humidity of about 90%.
Evaluation is carried out 12 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below.
TABLE 2
Venturia test (apple)/protective
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00110
 		1 1
Figure US08637534-20140128-C00111
 		1 0
According to the invention: found calc. *)
Figure US08637534-20140128-C00112
Figure US08637534-20140128-C00113
 		54 1
found = efficacy found
calc. = efficacy calculated using the Colby formula
EXAMPLE 3
Erysiphe Test (Barley)/Curative
Solvent:  10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
To test for curative activity, young plants are dusted with spores of Erysiphe graminis f.sp. hordei. 48 hours after the inoculation, the plants are sprayed with the active compound preparation at the stated application rate.
The plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.
Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below.
TABLE 3
Erysiphe test (barley)/curative
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00114
 		25 81
Figure US08637534-20140128-C00115
 		25 75
According to the invention:
Figure US08637534-20140128-C00116
Figure US08637534-20140128-C00117
 		100
EXAMPLE 4
Erysiphe Test (Barley)/Protective
Solvent:  10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration,
To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate.
After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f.sp. hordei.
The plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.
Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below
TABLE 4
Erysiphe test (barley)/curative
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00118
 		25 83
Figure US08637534-20140128-C00119
 		25 92
According to the invention:
Figure US08637534-20140128-C00120
Figure US08637534-20140128-C00121
 		100
Figure US08637534-20140128-C00122
Figure US08637534-20140128-C00123
 		100
Figure US08637534-20140128-C00124
Figure US08637534-20140128-C00125
 		100
EXAMPLE 5
Erysiphe Test (Wheat)/Curative
Solvent:  10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
To test for curative activity, young plants are dusted with spores of Erysiphe graminis f.sp. tritici. 48 hours after the inoculation, the plants are sprayed with the active compound preparation at the stated application rate.
The plants are then placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.
Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below.
TABLE 5
Erysiphe test (wheat)/curative
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00126
 		25   12.5  6.25 75 50 25
Figure US08637534-20140128-C00127
 		25   88
Figure US08637534-20140128-C00128
 		25   81
Figure US08637534-20140128-C00129
 		12.5  0
Figure US08637534-20140128-C00130
 		12.5  0
Figure US08637534-20140128-C00131
 		12.5  0
Figure US08637534-20140128-C00132
 		 6.25 38
Figure US08637534-20140128-C00133
 		 6.25 94
According to the invention:
Figure US08637534-20140128-C00134
Figure US08637534-20140128-C00135
 		100 
Figure US08637534-20140128-C00136
Figure US08637534-20140128-C00137
 		100 
Figure US08637534-20140128-C00138
Figure US08637534-20140128-C00139
 		100 
Figure US08637534-20140128-C00140
Figure US08637534-20140128-C00141
 		100 
Figure US08637534-20140128-C00142
Figure US08637534-20140128-C00143
 		100 
Figure US08637534-20140128-C00144
Figure US08637534-20140128-C00145
 		63
Figure US08637534-20140128-C00146
Figure US08637534-20140128-C00147
 		75
Figure US08637534-20140128-C00148
Figure US08637534-20140128-C00149
 		100 
Figure US08637534-20140128-C00150
Figure US08637534-20140128-C00151
 		100 
Figure US08637534-20140128-C00152
Figure US08637534-20140128-C00153
 		100 
Figure US08637534-20140128-C00154
Figure US08637534-20140128-C00155
 		75
Figure US08637534-20140128-C00156
Figure US08637534-20140128-C00157
 		50
Figure US08637534-20140128-C00158
Figure US08637534-20140128-C00159
 		100 
Figure US08637534-20140128-C00160
Figure US08637534-20140128-C00161
 		100 
EXAMPLE 6
Erysiphe Test (Wheat)/Protective
Solvent:  10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate.
After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f.sp. tritici.
The plants are then placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.
Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below.
TABLE 6
Erysiphe test (wheat)/protective
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00162
 		6.25 57
Figure US08637534-20140128-C00163
 		6.25 57
According to the invention:
Figure US08637534-20140128-C00164
Figure US08637534-20140128-C00165
 		79
Figure US08637534-20140128-C00166
Figure US08637534-20140128-C00167
 		71
Figure US08637534-20140128-C00168
Figure US08637534-20140128-C00169
 		71
EXAMPLE 7
Leptosphaeria nodosum Test (Wheat)/Protective
Solvent:  10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate.
After the spray coating has dried on, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain in an incubation cabin at 20° C. and 100% relative atmospheric humidity for 48 hours.
The plants are then placed in a greenhouse at a temperature of about 15° C. and a relative atmospheric humidity of about 80%.
Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below
TABLE 7
Leptosphaeria nodorum test (wheat)/protective
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00170
 		25 62
Figure US08637534-20140128-C00171
 		25 87
According to the invention:
Figure US08637534-20140128-C00172
Figure US08637534-20140128-C00173
 		100
EXAMPLE 8
Puccinia Test (Wheat)/Protective
Solvent:  10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
To test for protective activity, young plants are inoculated with a spore suspension of Puccinia recondite in a 0.1% strength aqueous agar solution. After the spray coating had dried on, the plants are sprayed with the active compound preparation at the stated application rate.
The plants remain in an incubation cabin at 20° C. and 100% relative atmospheric humidity for 24 hours.
The plants are then placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of rust pustules.
Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below.
TABLE 8
Puccinia test (wheat)/protective
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00174
 		25 38
Figure US08637534-20140128-C00175
 		25 94
According to the invention:
Figure US08637534-20140128-C00176
Figure US08637534-20140128-C00177
 		100 
Figure US08637534-20140128-C00178
Figure US08637534-20140128-C00179
 		100 
EXAMPLE 9
Fusarium culmorum Test (Wheat)/Seed Treatment
The active compounds are applied as a dry seed dressing. This is prepared by extending the respective active compound or the active compound combination with ground minerals to give a finely pulverulent mixture which ensures uniform distribution on the seed surface.
To dress the seed, the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.
2×100 corns of wheat are sown at a depth of 1 cm in standard soil and cultivated in a greenhouse at a temperature of about 18° C. and a relative atmospheric humidity of about 95% in seed trays which receive a light regimen of 15 hours per day.
About 3 weeks after sowing, the plants are evaluated for symptoms. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below.
TABLE 9
Fusarium culmorum test (wheat)/seed treatment
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00180
 		75 32
Figure US08637534-20140128-C00181
 		75 27
According to the invention:
Figure US08637534-20140128-C00182
Figure US08637534-20140128-C00183
 		41
EXAMPLE 10
Fusarium nivale Test (Triticale)/Seed Treatment
The active compounds are applied as a dry seed dressing. This is prepared by extending the respective active compound or the active compound combination with ground minerals to give a finely pulverulent mixture which ensures uniform distribution on the seed surface.
To dress the seed, the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.
2×100 corns of wheat are sown at a depth of 1 cm in standard soil and cultivated in a greenhouse at a temperature of about 10° C. and a relative atmospheric humidity of about 95% in seed trays which receive a light regimen of 15 hours per day.
About 3 weeks after sowing, the plants are evaluated for symptoms. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below
TABLE 10
Fusarium nivale test (triticale)/seed treatment
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00184
 		75 25 14  0
Figure US08637534-20140128-C00185
 		75 94
Figure US08637534-20140128-C00186
 		25  0
According to the invention:
Figure US08637534-20140128-C00187
Figure US08637534-20140128-C00188
 		99
Figure US08637534-20140128-C00189
Figure US08637534-20140128-C00190
 		31
EXAMPLE 11
Rhizoctonia solani Test (Cotton)/Seed Treatment
The active compounds are applied as a dry seed dressing. This is prepared by extending the respective active compound or the active compound combination with ground minerals to give a finely pulverulent mixture which ensures uniform distribution on the seed surface.
To dress the seed, the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.
2×50 corns of seed are sown at a depth of 2 cm in standard soil infected with Rhizoctonia solani, and the seeds are cultivated in a greenhouse at a temperature of about 22° C. in seed trays which receive a light regimen of 15 hours per day.
Evaluation is carried out after 8 days. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
Active compounds, application rates and test results are shown in the table below
TABLE 11
Rhizoctonia solani test (cotton)/seed treatment
Active compound
Active compound application rate in g/ha Efficacy in %
Known:
Figure US08637534-20140128-C00191
 		25 19
Figure US08637534-20140128-C00192
 		25 27
Figure US08637534-20140128-C00193
 		25  0
According to the invention:
Figure US08637534-20140128-C00194
Figure US08637534-20140128-C00195
 		40
Figure US08637534-20140128-C00196
Figure US08637534-20140128-C00197
 		31

Claims (10)

The invention claimed is:
1. A fungicidal composition comprising synergistically effective amounts of:
(a) a 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]2,4-dihydro-[1,2,4]-triazole-3-thione of the formula
Figure US08637534-20140128-C00198
and
(b) a compound of the formula
Figure US08637534-20140128-C00199
wherein the weight ratio of active compound of the formula (I) to the active compound of the formula (XII) is from 1:0.33 to 1:3.
2. The composition of claim 1 wherein the weight ratio of the active compound of formula (I) to the compound of formula (XII) is from 1:1 to 1:3.
3. The composition of claim 1 wherein the weight ratio of the active compound of formula (I) to the compound of formula (XII) is 3:1.
4. The composition of claim 1 wherein the weight ratio of the active compound of formula (I) to the compound of formula (XII) is 1:3.
5. The composition of claim 1 wherein the weight ratio of the active compound of formula (I) to the compound of formula (XII) is 1:1.
6. A method for controlling fungi comprising applying the composition according to claim 1 to the fungi and/or their habitat.
7. A method for controlling fungi comprising applying the composition according to claim 2 to the fungi and/or their habitat.
8. A fungicidal composition comprising synergistically effective amounts of:
(a) a 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]2,4-dihydro-[1,2,4]-triazole-3-thione of the formula of the formula
Figure US08637534-20140128-C00200
and
(b) a compound of the formula
Figure US08637534-20140128-C00201
wherein the weight ratio of active compound of the formula (I) to the active compound of the formula (XII) is from 1:1 to 3:1.
9. A method for controlling fungi comprising applying the composition according to claim 8 to the fungi and/or their habitat.
10. A fungicidal composition comprising synergistically effective amounts of:
(a) a 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]2,4-dihydro-[1,2,4]-triazole-3-thione of the formula
and
(b) a compound of the formula
wherein the weight ratio of the active compound of formula (I) to the compound of formula (XII) is 1:5.
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